P
US6548553B2ExpiredUtilityPatentIndex 92

Styryl sulfone anticancer agents

Assignee: UNIV TEMPLEPriority: Oct 3, 1997Filed: Jul 31, 2001Granted: Apr 15, 2003
Est. expiryOct 3, 2017(expired)· nominal 20-yr term from priority
Inventors:REDDY E PREMKUMARREDDY M V RAMANA
C07C 317/10C07C 317/14
92
PatentIndex Score
26
Cited by
31
References
27
Claims

Abstract

Styryl sulfone compounds of the invention selectively inhibit proliferation of tumor cells, and induce apoptosis of tumor cells, while sparing normal cells. The compounds, which are useful in the treatment of cancer and other proliferative disorders, have(a) the formula II: wherein n is zero or one; R1 is selected from the group consisting of hydrogen, chlorine, fluorine and bromine; R2 is selected from the group consisting of hydrogen, chlorine, fluorine, bromine, methyl and methoxy; and R3 is selected from the group consisting of hydrogen, chlorine and fluorine; provided, R2 may not be methyl or methoxy when R1 and R3 are both hydrogen and n is zero or one; and R1, R2 and R3 may not all be hydrogen when n is one;(b) the formula III: wherein R1 is selected from the group consisting of hydrogen, chlorine, fluorine and bromine; or(c) or the formula IV: wherein R1 is selected from the group consisting of fluorine and bromine, and R2 is selected from the group consisting of 2-chlorophenyl, 4-chlorophenyl, 4-fluorophenyl and 2-nitrophenyl.

Claims

exact text as granted — not AI-modified
What is claimed is:  
     
       1. A method of treating an individual for a cancer other than prostate or breast cancer comprising administering to said individual an effective amount of a compound of formula II                    
       wherein 
       n is zero or one;  
       R 1  is selected from the group consisting of hydrogen, chlorine, fluorine and bromine;  
       R 2  is selected from the group consisting of hydrogen, chlorine, fluorine, bromine, methyl and methoxy; and  
       R 3  is selected from the group consisting of hydrogen, chlorine and fluorine; provided,  
       R 2  may not be methyl or methoxy when R 1  and R 3  are both hydrogen and n is zero or one; and  
       R 1 , R 2  and R 3  may not all be hydrogen when n is one.  
     
     
       2. The method according to  claim 1  wherein the compound is E-4-bromostyryl phenyl sulfone. 
     
     
       3. The method according to  claim 1  wherein the compound is E-2,4-difluorostyryl 4-fluorobenzyl sulfone. 
     
     
       4. The method according to  claim 1  wherein the compound is E-2-chloro-4-fluorostyryl 4-chlorobenzyl sulfone. 
     
     
       5. The method according to  claim 1 , wherein R 3  is hydrogen, and R 1  and R 2  are independently selected from the group consisting of chlorine, fluorine and bromine. 
     
     
       6. The method according to  claim 5  wherein the compound is E-4-chlorostyryl 4-chlorophenyl sulfone. 
     
     
       7. The method according to  claim 5  wherein the compound is E-4-bromostyryl 4-chlorophenyl sulfone. 
     
     
       8. The method according to  claim 5  wherein the compound is E-4-fluorostyryl 4-chlorobenzyl sulfone. 
     
     
       9. The method according to  claim 5  wherein the compound is E-4-chlorostyryl 4-chlorobenzyl sulfone. 
     
     
       10. The method according to  claim 5  wherein the compound is E-4-fluorostyryl 4-fluorobenzyl sulfone. 
     
     
       11. The method according to  claim 5  wherein the compound is E-4-fluorostyryl 4-bromobenzyl sulfone. 
     
     
       12. The method according to  claim 5  wherein the compound is E-4-bromostyryl 4-bromobenzyl sulfone. 
     
     
       13. The method according to  claim 5  wherein the compound is E-4-bromostyryl 4-fluorobenzyl sulfone. 
     
     
       14. The method according to  claim 5  wherein the compound is E-4-chlorostyryl 4-bromobenzyl sulfone. 
     
     
       15. The method according to  claim 5  wherein the compound is E-4-bromostyryl 4-chlorobenzyl sulfone. 
     
     
       16. The method according to  claim 1  wherein the cancer is selected from the group consisting of cancers of the ovaries, lung, colon, rectum, brain, kidney, pancreas and skin; leukemias; lymphomas; sarcomas; squamous cell carcinomas and papillomas; basal cell carcinomas and papillomas; and epidermoid cancers. 
     
     
       17. The method according to  claim 16  wherein the compound is selected from the group consisting of (E)-4-fluorostyryl-4-chlorobenzyl sulfone, (E)-4-fluorostyryl-4-bromobenzyl sulfone, (E)-4-chlorostyryl-4-bromobenzyl sulfone and (E)-2-chloro-4-fluorostyryl-4-chlorobenzyl sulfone. 
     
     
       18. A method of inhibiting the growth of tumor cells in an individual afflicted with cancer, other than breast or prostate tumor cells, comprising administering to said individual an effective amount of a compound of formula II                    
       wherein 
       n is zero or one;  
       R 1  is selected from the group consisting of hydrogen, chlorine, fluorine and bromine;  
       R 2  is selected from the group consisting of hydrogen, chlorine, fluorine, bromine, methyl and methoxy; and  
       R 3  is selected from the group consisting of hydrogen, chlorine and fluorine; provided,  
       R 2  may not be methyl or methoxy when R 1  and R 3  are both hydrogen and n is zero or one; and  
       R 1 , R 2  and R 3  may not all be hydrogen when n is one.  
     
     
       19. A method according to  claim 18  wherein the inhibition of growth of said tumor cells includes inducing apoptosis of tumor cells. 
     
     
       20. A method of treating an individual for a cancer other than prostate or breast cancer comprising administering to said individual an effective amount of a compound of formula III                    
       wherein R 1  is selected from the group consisting of hydrogen, chlorine, fluorine and bromine. 
     
     
       21. The method according to  claim 20  wherein the cancer is selected from the group consisting of cancers of the ovaries, lung, colon, rectum, brain, kidney, pancreas and skin; leukemias; lymphomas; sarcomas; squamous cell carcinomas and papillomas; basal cell carcinomas and papillomas; and epidermoid cancers. 
     
     
       22. A method of inhibiting the growth of tumor cells in an individual afflicted with cancer, other than breast or prostate tumor cells, comprising administering to said individual an effective amount of a compound of formula III                    
       wherein R 1  is selected from the group consisting of hydrogen, chlorine, fluorine and bromine. 
     
     
       23. A method according to  claim 22  wherein the inhibition of growth of said tumor cells includes inducing apoptosis of tumor cells. 
     
     
       24. A method of treating an individual for a cancer other than prostate or breast cancer comprising administering to said individual an effective amount of a compound of formula IV                    
       wherein R 1  is selected from the group consisting of fluorine and bromine, and R 2  is selected from the group consisting of 2-chlorophenyl, 4-chlorophenyl, 4-fluorophenyl and 2-nitrophenyl. 
     
     
       25. The method according to  claim 24  wherein the cancer is selected from the group consisting of cancers of the ovaries, lung, colon, rectum, brain, kidney, pancreas and skin; leukemias; lymphomas; sarcomas; squamous cell carcinomas and papillomas; basal cell carcinomas and papillomas; and epidermoid cancers. 
     
     
       26. A method of inhibiting the growth of tumor cells in an individual afflicted with cancer, other than breast or prostate tumor cells, comprising administering to said individual an effective amount of a compound of formula IV                    
       wherein R 1  is selected from the group consisting of fluorine and bromine, and R 2  is selected from the group consisting of 2-chlorophenyl, 4-chlorophenyl, 4-fluorophenyl and 2-nitrophenyl. 
     
     
       27. A method according to  claim 26  wherein the inhibition of growth of said tumor cells includes inducing apoptosis of tumor cells.

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